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Artigo Revisado por pares
BIBTEX RIS

Azidoperfluoroalkanes: Synthesis and Application in Copper(I)‐Catalyzed Azide–Alkyne Cycloaddition

2016; Wiley; Volume: 56; Issue: 1 Linguagem: Inglês

10.1002/anie.201609715

ISSN

1521-3773

Autores

Zsófia E. Blastik, S. Voltrová, Václav Matoušek, Bronislav Jurásek, David W. Manley, Blanka Klepetářová, Petr Beier,

Tópico(s)

Cyclopropane Reaction Mechanisms

Resumo

Abstract We report an efficient and scalable synthesis of azidotrifluoromethane (CF 3 N 3 ) and longer perfluorocarbon‐chain analogues (R F N 3 ; R F =C 2 F 5 , n C 3 F 7 , n C 8 F 17 ), which enables the direct insertion of CF 3 and perfluoroalkyl groups into triazole ring systems. The azidoperfluoroalkanes show good reactivity with terminal alkynes in copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC), giving access to rare and stable N ‐perfluoroalkyl triazoles. Azidoperfluoroalkanes are thermally stable and the efficiency of their preparation should be attractive for discovery programs.

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